Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides

Bioorg Med Chem Lett. 2006 Jul 15;16(14):3663-7. doi: 10.1016/j.bmcl.2006.04.067. Epub 2006 May 8.

Abstract

A series of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides (2a-z) was obtained by reacting 6,7-dihydro-1H-imidazo[2,1-c][1,2,4]thiadiazol-3-thione (1) with arylsulfonyl chlorides. The relationships between structure and anti-tumor activity revealed that compound 2o with p-Cl substituent at the phenyl ring was most active (-log GI50>8.00, -log TGI=7.66) and was found to exhibit high selectivity toward the leukemia CCRF-CEM cell line (Deltaf=3.08 and 3.31, respectively).

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Humans
  • Inhibitory Concentration 50
  • Leukemia, Lymphoid / metabolism
  • Leukemia, Lymphoid / pathology
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology*
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / pharmacology*

Substances

  • Antineoplastic Agents
  • Sulfonamides
  • Thiadiazoles